


Errant Gambles

by Mirradin



Category: Homestuck
Genre: Anal Sex, Biting, Cunnilingus, Desk Sex, F/M, Face-Sitting, M/M, Multi, Oral Sex, Rough Sex, Self-Sacrifice, The Homestuck Epilogues
Language: English
Status: Completed
Published: 2019-07-14
Updated: 2019-07-14
Packaged: 2020-05-19 13:29:02
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 4,021
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19357963
Author URL: https://archiveofourown.org/users/Mirradin/pseuds/Mirradin
Summary: President Jane and her chief advisor Dirk are planning a brutal end to the rebellion. Jake distracts them. With his body.





	Errant Gambles

**Author's Note:**

  * For [RoseWithAllHerThorns](https://archiveofourown.org/users/RoseWithAllHerThorns/gifts).



He’s put Tavros to bed early. The lad sleeps like a lamb these days, right through to morning without a peep, and his nursery’s on the other side of Jake’s room besides, no need to worry about him waking up. Jane put some excellent soundproofing in; even if he does wake up he won’t hear a thing.

Jake wishes he hadn’t had to leave his skulltop and phone in the nursery, one tucked between some books and the other stowed hastily under the bed, only he sent some rather, ah, _incriminating_ messages in a hurry a few minutes ago, and he’d really rather Jane not see them. Besides, if someone replied he’s not sure he could keep either of them from seeing who he’s been talking to. Best keep his communications well out of the way, even if that risks disturbing Tavros’s sleep a little. He hopes they don’t disturb Tavros, but it is a risk, even though Jake did his best to turn the alerts off.

He fiddles with the collar of his shirt. One button undone or two? Jane always likes to see more of him then he’s strictly comfortable with, but he can’t quite remember if Dirk ever expressed a preference, it was so bally long ago. He can’t rightly recall that he ever worried much about it when he used to go out on dates, but then the stakes were a darn sight lower back then.

Well, there’s no point being shy, they’re going to see a lot more of him than a flash of bare chest in a bit! Jake breathes in and flicks the second button open. There! Nice and suggestive, that should start them all off on the right foot.

He opens the door.

“Ah! There you are!” he says brightly. Jane and Dirk look up from the laptops and papers spread over Jane’s desk. Jake smiles as widely as he can. “I’ve been looking all over for you!”

“We’re busy,” Jane says. “Running the world _does_ take a lot of work, Jake.”

“Er, I suppose so…” He swallows. Tries for a flirtatious tone (he isn’t sure it’s working). “I was hardly expecting  you to still be at it at this time of night, though!”

“We’re important people,” Dirk says blandly.

“Do you _want_ something, Jake?” Jane demands.

It’s an opening. Jake takes the plunge.

“Well…” He nudges the door shut. “I was hoping we could spend some time together.” He smiles at her again; it feels awkward, but Jane’s frown softens. “I haven’t seen much of you lately. I thought it would be nice to, er, catch up? Just the three of us.” Cripes, was that obvious enough? “You know, privately.”

He crosses his fingers behind his back. It wouldn’t be the first time he’s slept with two of his friends at once, Jade and Roxy are both very friendly people, but that’s no guarantee that Dirk and Jane will be particularly interested. As he recalls, Jane used to think Dirk was a fine figure of a man, but if either of them declines he doesn’t know what he’s going to do next, and then Jade and the rebellion…

Jane looks thoughtful. Jake takes a chance and crosses the room to lean on the desk. He doesn’t usually do this, Jane tends to initiate things more than he does –but she doesn’t seem to mind. Her eyes linger on his open shirt, and she smiles.

“A break would be nice,” she says. “If you’re interested, Mr Strider?”

“Tempting,” Dirk says. “But unfortunately we do have important shit to get done, so –”

“Can’t it wait?” Jake perches gingerly on the corner of the desk. “You both work like the dickens, surely it won’t hurt if you take one night off!”

“You don’t know anything about it,” Jane snaps, and Jake’s stomach does a queasy roll. “But an hour or so won’t make any difference,” she adds. “If the analysis is accurate –”

“Of course it’s accurate. I did it.”

“Well, then!” Jake offers Dirk his brightest grin. “Come to bed.”

Jane grabs his arm and pulls. Jake nearly falls flat on the desk, but manages to scramble over it so that Jane can pull him onto her lap for a kiss.

“No need to go that far,” she murmurs against his lips, as her hands unbutton his shirt. “The table should be big enough.”

“Er, I suppose so-” Jake shifts uncomfortably as her knuckles drag over his abdomen. “It’s not as comfortable, is it though?”

“Jake,” Jane says severely, “are you arguing with me?”

His stomach twists. “No, dear.”

The chair behind him creaks, and Dirk’s hands land on his shoulders. “That simple, huh?” Dirk comments.

“We’ve had a while to work things out.” Jane pushes his shirt open, her fingers gliding along his collarbones. “He learned eventually.” She shoves his shirt back over his shoulders. Jake feels Dirk’s fingers tighten in the fabric, and puts his arms back so Dirk can pull it off.

Neither of them likes waiting around, as a rule, and now is no different. The second his shirt comes off, Jane’s hands are on his rear, kneading away. Dirk drops the shirt on the floor and presses up against Jake’s back, sliding a hand down his belly to his fly. Jake braces one hand on the arm of the chair and loops the other arm loosely around Jane’s shoulders. Sometimes she likes it when he strokes her neck, so he does that, and Jane grabs his hair to pull him into another kiss. It’s deep and fierce, and Jake’s body starts responding.

That’s a good thing, he reminds himself. She likes him to want her. He needs her to want him.

“Mind if I mark him up?”

Jane breaks the kiss to lean back – Jake hastily drops his arm from her shoulders – and gives him a long, indulgent once-over. Jake straightens up to give her a better view, as much as he can with Dirk hanging off him like a cape, and Jane’s smile widens. “Mmm, yes. Please.”

Should he say something? Agree, maybe? Or –

Dirk’s mouth on his neck isn’t much of a shock. The fellow always did have a bit of a thing for love bites, got a bit of a bee in his bonnet when Jake used to cover them up back in the Game – Dirk’s teeth graze his skin and Jake loses track of that thought. Then Dirk catches his skin between his teeth, tugging at it, and Jake’s breath hitches.

 _Go easy there,_ he almost says – but he can’t. Jane’s watching him with dark, appreciative eyes, and Dirk is, well, _hopefully_ enjoying himself, and Jake needs to keep them happy rather more than he ever has. What’s a few love bites to that?

So he tips his head to the side a bit, makes it easier for Dirk to get at him. Dirk hums against his neck, and _thank jegus_ stops nibbling on him like a cat. Jake relaxes back against him, and Dirk works his way down Jake’s neck to the crook of his shoulder, leaving a cold trail in his wake.

“He smells good, doesn’t he?” Jane says.

“Tell me about it,” Dirk replies, his voice muffled in Jake’s shoulder. “I spent an inordinate amount of time wrestling him.” His teeth scrape over Jake’s skin again, and Jane bursts out laughing.

“I believe you set yourself up there, Mr Strider,” she says between giggles.

“In retrospect that might not have been one of my best decisions,” Dirk says, pulling back. “Hmm.”

Before Jake can ask what _that_ means, Dirk’s mouth is back, and this time he clamps his teeth around the meat of Jake’s shoulder and bites down _hard._

Jake can’t help yelping and jerking away – it’s not the first time one of his partners has bitten him, several charming trolls he passed an evening with had a habit of chomping on him when they got into the spirit of things, and their teeth were a sight sharper than Dirk’s are, it’s just that he wasn’t expecting it from Dirk, and it’s a bit of a shock. He doesn’t usually seeking out. His thrashing doesn’t help in any event; Dirk’s teeth are sunk in him firmly and all Jake manages is to make it hurt worse.

“Warn a chap next time, would you?” he gasps, and Dirk finally lets go.

“What, you don’t _like_ that?” This time he bites the nape of Jake’s neck, and it’s not so much of a shock – he flinches, but manages not to pull away. Dirk holds on for a second before releasing him.

“I’m not complaining,” he insists, although he rather wishes he could. “Just, ah – if you wouldn’t mind saying something first -?”

Jane rolls her eyes and runs her fingers over the bitemark on his shoulder. “Oh, don’t complain so much, Jake. It looks good. Turn your head – no, the other way.”

She doesn’t bite down as hard as Dirk did, but she lingers after, sucking hard until he feels blood rush to the skin. Dirk groans softly in his ear. He’s back to fingering Jake’s belt, and it feels mighty intentional.

Good, he reminds himself. That’s a good thing.

“ _Fuck_ that’s hot,” Dirk says when she pulls back.

“Thank you.” Jane sits backs and looks him over again. Her hair is a tad dishevelled. She’s a fine figure of a woman, even if she is a tad forceful, and, well, a bit prone to overreaction sometimes. And, er, also war crimes. (Please, please, if there’s anything out there, let those messages have gone through -) “Now everyone will know who you belong to,” she muses.

Jake swallows hard. This is new. Dirk is pressed up against his back, and he’s certainly roused and ready to go. “I thought everyone knew that already, dearest?”

Jane rolls her eyes. “Of course everyone knows you’re _mine_ , Jake. I meant this.” She flicks the spot Dirk bit.

“Is that an offer?” Dirk asks, half wary, half teasing.

“It might be,” Jane murmurs. Her eyes are playful. Jake can’t remember the last time she looked that way in his general direction. He wasn’t even sure she _could_ look that way anymore, but it seems she can, and she looks so much like her old self he wants to cry.

“Well, in that case.” Dirk’s voice turns sardonic and formal. “Miss Crocker. May I take this fine stud of yours for a ride?”

 “Why, Mr Strider!” Jane tips her head back as if she’s shocked, sweeps her hand out grandly. “Please, be my guest.”

“Hell yes.” Dirk nips the top of Jake’s ear. “Let’s take this to the table.”

He steps back. Jake climbs out of Jane’s lap. His legs don’t feel terribly steady, but that’s all right, they won’t need to hold him for very long. Just long enough to blink back the tears he doesn’t dare shed, and try to look willing, and turn to Dirk.

“How do you want me?”

He thinks Dirk looks him over, but it’s blessed hard to tell, behind those shades of his. “Ditch the pants and turn around.”

Well, he can manage that.

It takes him a couple of goes to get the zipper of his fly down, and the button won’t cooperate at all; he ends up popping it clean off. At least it lets him shove his shorts down. Jake kicks them off under the table and bends over it, leaning his elbows on the neat lines of paperwork. _INTELLIGENCE REPORT,_ one of them reads. There’s a map of a valley he and Jade once spent a week hiking through, and a pile of military reports, and pages of notes in Jane’s and Dirk’s handwriting.

“I missed this.” Dirk’s hand lands between his shoulder blades and slides down, following the curve of his spine. When he reaches Jake’s rear he gets a handful and squeezes. Coming from Dirk it feels like a conquest, rather than Jane’s casual possessiveness. “You’re gorgeous. Where’s the lube?”

Jake’s hands curl up, crumpling the map. “In the bedroom,” he admits.

The hand gripping his buttock relaxes slightly. “In the bedroom,” Dirk echoes.

“Jake!” It’s the tone that means Jane’s rolling her eyes. Jake flinches. “Did you really interrupt us and not even come prepared? Honestly.”

“I’m sorry –”

“Yeah, I’m sure you are,” Dirk cuts him off. “Unfortunately, you being sorry is not exactly helpful here.”

Jake swallows. His throat is dry. “I could suck your fingers,” he offers.

Pause. “Why should I let you?” Dirk asks. He steps closer and then his clothed cock is pressed up against Jake’s bare arse, a bulge that rubs over his crack when Dirk rocks his hips. “That sounds a lot like rewarding you for bad planning.”

Oh holy Mary, sinners and saints. Jake goes cold all over. Dirk’s words shiver down his spine and start his legs trembling, and if he wasn’t bent over the desk he might have trouble staying on his feet. He didn’t know. Jumping Josaphat, he didn’t know. He knew all along that this could hurt, they both like to play rough and he wasn’t foolish enough to think they might not take out their frustrations on him, but that’s always been like the biting, something done for pleasure, and he didn’t think –

He never knew Dirk would want to hurt him for the sake of hurting him, and not just because it was how the man liked his bedsport.

“Please,” he begs. Dirk’s hand on his rear feels horribly intent. “It – it won’t feel as good dry, Dirk, it’ll be easier if I wet you up a little, won’t it? You can move easier if I – I know how you like it,” because he has a wild memory of sucking Dirk’s fingers back in the Game, and Dirk told him back then what he liked _,_ “I’ll do it properly, I can – please?”

Jane draws her breath in sharply, and Jake hears the chair roll back as she stands up and comes around the table. She crouches down across from him to put them on the same level. Jake can feel tears welling up, can’t even start trying to muster a smile, but Jane doesn’t seem to mind one whit.

“Is that all?” Dirk asks. He lets go of Jake’s buttock, and starts drawing his finger lazily down the cleft of his arse instead.

Jake tries to think of something else, anything else, and comes up blank. Jane’s watching him avidly, and all he can think is that she might enjoy watching him cry. Dirk doesn’t seem to care either way. He doesn’t know what to say to these people who look like his old friends. Maybe he never knew them at all.

“Anything else?” Dirk prompts.

“ _Please_ ,” Jake whispers.

“You remember what I like?” Dirk takes that hand off his rear and leans forward so he can reach Jake’s mouth. “Prove it.”

Dirk’s fingers are long and slender, rough with calluses. Jake opens his mouth and takes them in.

Back in the Game, Dirk told him to lick down each finger, to work his tongue into the space between. Jake does that now, tasting salt and an odd mustiness that must be from the paperwork. The angle’s all wrong for him to take them down to the knuckle, but Jake sucks them in as far as he can, tracing the joints with the tip of his tongue. The edge of a fingernail digs into his soft palate, and he struggles not to gag. This is all the slick he’s getting.

He does his best, but Dirk pulls his fingers back out after what feels like far too short a time. Jake coughs painfully, miserably certain that it’s not going to be enough.

Dirk doesn’t give him any warning before breaching him with two fingers at once, shoving hard to get past the resistance of his body. Jake closes his eyes and breathes in shakily. It hurts – Dirk’s fingers really aren’t wet enough, and he’s not being gentle – but not as much as being bitten did. It’s bearable.

But it’s a horribly intimate pain, and it gets worse when Dirk turns his wrist and rubs over a specific place inside him. Jake jerks forward without meaning to. It feels like lightning inside him – it feels _good_. Jake’s guts are knotted up with fear, and he doesn’t know why he thought that would make a difference, but he did and it doesn’t. It still feels good.

Dirk pulls him back with a hand on his hip and does it again. He’s always had a knack for finding that – he was the one who _introduced_ Jake to that, over a decade ago, and it looks like he hasn’t forgotten how Jake’s body responds to it. Probably he hasn’t forgotten anything about Jake’s body, or anything he learned while they were sharing a bed. Dirk always was a tad obsessive about mastering his hobbies.

And it’s working. Jake can’t be as grateful as he should, but it’s working. He’s opening up more with every jolt of pleasure, even as his cock stirs unwillingly. The pain’s easing, and that has to be better, doesn’t it? If it hurts less – and if it keeps Dirk and Jane happier, that has to be good too. Doesn’t it?

It’s still a relief when Dirk pulls his fingers out, even knowing what’s coming.

He hears Dirk pull his zipper down, and opens his eyes to stare at the map under his forearms. There’s a red star stuck to one end of a valley he and Jade hiked through once, ten years ago. Nice place, roomy and dry, fairly out of the way. A good place for a rebellion to set up camp.

Dirk grips his shoulder, and then his cock is pushing in hard and fast, driving the breath out of him. Jake chokes on a yelp, his fingers scrabbling through the paperwork. Jane’ll be angry if he rips something. He links his fingers together and squeezes, hard, biting his lip as Dirk’s thrusts drive his hips up against the edge of the desk.

Dirk doesn’t take it slowly. He fucks Jake hard, steadily, like a machine. The edges of his open zipper chafe against Jake’s rear every time Dirk sinks in. Jake isn’t relaxed enough, and every thrust is a burning, pinching pain that has him gasping for breath.

He realises he’s crying again when the tears land on his arm, and feels another thrill of fear. No, wait, Jane doesn’t like him crying, doesn’t approve of him “carrying on”, he needs to –

“Enjoying the show?” Dirk says over his head.

“Oh, yes. Very much so.” Jake manages to lift his head, to find Jane watching them both hungrily. “You’re good at this.”

Dirk laughs breathlessly. “Thanks. How does he look?”

“Very good. He’s crying.”

Dirk shoves in _hard_ , and Jake pitches forward, the map sliding under his elbows. “Already?”

“Like he’s at a funeral,” Jane confirms.

Dirk pulls out abruptly. “Turn around.”

Jake pushes himself up clumsily, and does as he’s told. He can’t look Dirk in the face, until Dirk orders “ _Look at me_ ,” and Jake reluctantly drags his eyes up.

Dirk doesn’t look so inscrutable now. His face is flushed, and there’s a sheen of sweat at his temples. His mouth quirks up as he studies Jake, the tear-tracks down his cheeks and the way his mouth is trembling.

“Nice,” he says quietly. “I should get you to cry more often.”

There’s nothing Jake can say to that, so he doesn’t even try. Dirk studies him a moment longer, then looks past him. “Hey, Jane, do you want a turn?”

“Oh, no, please. It’s nice to watch. I’ll have his mouth when you’re done.”

Dirk’s smile turns more genuine. “How about I put him on his back? That way you can ride his face and watch at the same time.”

“Oooh,” Jane says, delighted. “I like the way you think, Mr Strider.”

At Dirk’s raised eyebrow, Jake climbs back onto the table, lying back among the paperwork. He lifts his legs up without prompting so that Dirk can step between them, flinching when Dirk catches his ankle and lifts it higher. Jane fumbles with her trousers, kicks off her shoes, and then the light is blotted out by her climbing onto the table.

She’s wet. This close to her, he can see it – he can _smell_ it from here, the familiar musk of her arousal, and his cock twitches in response. They’ve been sharing a bed for years, now; he knows her scent better than anyone else’s. It gets stronger when she settles herself over his face, and he opens his mouth to lick at her obediently. His world narrows down to Jane: Her scent in his nose, her taste on his tongue, her body blotting out sight, and her legs around his ears. All that’s left to him is touch.

Dirk pushes back into him. Jake closes his hands.

He can hear the two of them talking over him, but Jane’s legs muffle their voices into nonsense. All he has to go on is the way they touch him – Dirk’s grip on his ankle, Jane’s hands on his chest, and the way both of them move their hips.

He does his best. He works his tongue over Jane the way she likes it, circles he clit, sucks gently. She grinds down on his face until his cheeks are wet with her arousal. He works his tongue up into her and she bucks like she likes it. Once her body tightens up and shudders with laughter.

Neither of them touches his cock. It’s a thin bit of relief.

Dirk’s thrusts speed up and go ragged, and then there’s a sudden wetness inside him. Jane grinds down harder, and Jake sucks in a breath and goes back to flicking his tongue over her clit as Dirk rocks into him, riding out the aftershocks.

It doesn’t take long for Jane to get to the edge after that. Dirk stays inside him the whole time, idly stroking his ankle. Jane rocks down on him until he thinks he’ll suffocate, legs locking tight as it builds, and then she’s shuddering over him and lifting away and his sight comes rushing back and it’s over, it’s done, he pleased her and he’s done.

“Not bad,” Jane says breathlessly, climbing off him. Dirk pulls back, leaving Jake empty and cold, and starts tucking himself away. “We’ll have to do that again some time.”

There’s a clock over the door, very smart, with the numbers in a no-nonsense blocky script. It’s easy to read, even upside-down.

Ten past eleven.

Half an hour. Has it really only been that long? Will it be enough? For people to move by helicopter and on foot, surely not, but for a Witch of Space –

Jake makes himself sit up, dredges up a smile. “Yes, dear. I’d like that.”

Dirk raises an eyebrow at him, and Jake’s smile wavers. After a moment, Dirk’s mouth curls up. “Sure. It was fun.”

“Some other time,” Jane says firmly. She glances at the clock. “Oh, for heaven’s sake – Jake, get out. We’re late. I’ll see you later.”

Half an hour, Jake thinks numbly, gathering up his clothes and stumbling to the door. It doesn’t seem like long enough for all of that. Surely everything they did to him should have bought more time than a mere half an hour.

He washes himself in the master bedroom’s en-suite, thoroughly scrubbing Jane’s slickness from his face and Dirk’s seed from his rear, until his skin is pink and raw. Then he finds a high-necked shirt to cover the bruises and slips into Tavros’s room. The lad’s already asleep, curled up like a kitten, and Jake retrieves his phone before slumping down by the bed.

**GT: Jade you need to evacuate!**

**GT: Your base is about to get firebombed!**

**GT: Ill try to delay them but you need to get out of there pronto!**

**GG: were on it!**

**GG: what do you mean delay them??**

**GG: JAKE??**

**End.**


End file.
